Diisopropylethylamine → HCID 22643352, compound

HRID 2414813Notes

Reaction equation

HRID 2414813 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH2:13])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23](O)=[O:24])=[CH:17][CH:16]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([CH2:11][CH2:12][NH:13][C:23](=[O:24])[CH2:22][CH2:21][C:18]2[CH:19]=[CH:20][C:15]([F:14])=[CH:16][CH:17]=2)[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1363023-(4-Fluorophenyl)propionic acidHCID 1378573,5-DimethoxyphenethylamineHCID 2724699PyBOP

Product 1

HCID 22643352HCID 22643352, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-(3,5-Dimethoxy-phenyl)ethylamine (1.20 g, 6.62 mmol) is dissolved in anhydrous DMF (50 mL), and 3-(4-fluorophenyl) propionic acid (1.113 g, 6.62 mmol), PyBOP (3.77 g) and DIPEA (2.61 mL, 15 mmol) are added. The mixture is stirred at rt for 14 h. Water (60 mL) is added, and the mixture is extracted with EtOAc (4×60 mL). The combined organic phases are washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by silica gel column chromatography (EtOAc/Hex, 7:3) to afford the title compound as a yellow oil.

Workup

  1. extractionthe mixture is extracted with EtOAc (4×60 mL)
  2. washThe combined organic phases are washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by silica gel column chromatography (EtOAc/Hex, 7:3)

Sources & evidence

ORD record
ord-7a88880bf7944391b0b3ba849e717eb7
Source dataset
uspto-grants-2004_11
Patent number
US06815451B2

Reaction notes

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